MIPs logo MIPdatabase      Use this space
Custom Search
Reference type: Journal
Authors: Takeda K, Kuwahara A, Ohmori K, Takeuchi T
Article Title: Molecularly Imprinted Tunable Binding Sites Based on Conjugated Prosthetic Groups and Ion-Paired Cofactors.
Publication date: 2009
Journal: Journal of the American Chemical Society
Volume: 131
Issue: (25)
Page numbers: 8833-8838.
DOI: 10.1021/ja9004317

Abstract: A molecular imprinting technique was applied to the construction of prosthetic group-coupled tunable binding cavities for bisphenol A (BPA). A novel template molecule, with a structure consisting of BPA covalently conjugated with two allyl(4-carboxyphenyl)disulfides through ester bonds (BPA-D), was designed. After copolymerization of BPA-D with styrene and divinylbenzene, the BPA di(4-mercaptobenzoate) moieties were removed by reductive cleavage of the disulfide bonds, resulting in apo-type molecularly imprinted cavities bearing two thiol residues. 4-Mercaptobenzoic acid was introduced into the apo-type cavities as a prosthetic group through a disulfide bond by addition of 4,4GǦ-dithiodibenzoic acid, which transformed the apo-type cavities into holo-type cavities with two carboxylic acid residues for binding BPA. When pyridyl prosthetic groups were introduced instead of 4-mercaptobenzoic acid by using 4,4GǦ-dithiodipyridine, BPA recognition ability was maintained but with improved selectivity. The binding affinity was successfully altered several times by attaching and detaching these prosthetic groups, which showed that the apo-type scaffold could be reused. Furthermore, noncovalent-type ion-paired cofactors could be introduced, when the two thiol groups in the apo-type cavities were oxidized to sulfonic acid groups. When 1,2-diaminoethane (DAE) was added to the oxidized apo-type scaffold as a noncovalent-type cofactor, the binding activity was regulated successively, depending upon the concentrations of DAE added. By using various prosthetic groups and cofactors, the binding properties of the holo-type cavities could be tuned in a similar way to those found in biological systems
Template and target information: bisphenol A, BPA, bisphenol Adi(4-mercaptobenzoate)

  Eat, sleep, imprint, repeat shirt  SMI logo mug    Mug featuring the template Bisphenol A

Molecules Special Issue call      Appeal for information


Join the Society for Molecular Imprinting
Logo of the Society for Molecular Imprinting

New items RSS feed
new items RSS feed  View latest updates

Sign-up for e-mail updates:
Choose between receiving an occasional newsletter or more frequent e-mail alerts.
Click here to go to the sign-up page.

Is your name elemental or peptidic? Enter your name and find out by clicking either of the buttons below!
Other products you may like:
view listings for MIP books on eBay:

Mickey Mouse 90th Anniversary banner